How traveling can make you a better CEO

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Originally published in American City Business Journals

By Jen O’Neal

When friends tell me they want to start a company, I tell them to travel the world first.

Becoming an entrepreneur is like taking a gigantic, flying leap out of your comfort zone and into the vast unknown. Travel, too, mandates that you quite literally step outside your comfort zone.

More often than not, navigating through unfamiliar foreign territory will teach you the same skills that you need to run a successful business. Travel has not only allowed me to see the world, but it also has helped me become a better leader and a better CEO.

Bartering with quick-talking shop owners in the open markets of Paris taught me how to negotiate. Doing currency calculations in my head allowed me to sharpen my math skills.

Missing planes taught me patience. Being stranded without cash taught me how to be creative. And traveling in big groups taught me how to keep everyone happy while — most of the time — keeping everyone on schedule.

Here are some of the other skills I’ve learned on the road that I leverage daily in my life as a startup founder.

1. Contingency planning

I once arrived at the Munich Hauptbahnhof (train station) only to learn that a strike had canceled all trains leaving the country. I had unwisely spent the last of my Deutsche Marks before reaching the station, and local banks were closed for the day. I was stuck there alone with no money, no food and no place to stay.

It was a rookie mistake. I hadn’t considered the possibility that a strike could leave me stranded. Now when I travel, I carry cash in several different currencies. I also double-check to make sure transportation is running on time and I always have a backup plan in case something goes wrong.

Contingency planning is a critical part of running a successful company. When I raise funding, I make sure to have several term sheets in hand so we have options in case one of them doesn’t pan out.

When we launch a new product, we have a backup plan in case the product doesn’t perform. And when I make an offer to a candidate, I typically have a few other candidates waiting in the wings. The point is that whether you’re traveling the world or running a company, you always need to plan ahead and be prepared for all outcomes.

2. Patience

The tongue-tying sensation of not knowing the language when you’re in a foreign country highlights humankind’s many differences. Being unable to communicate is incredibly humbling; it forces you to rely on the kindness of strangers who are willing to play charades with you as you fumble in your attempts to ask for directions or order off a menu.

Because of this, I’m more patient when we hire someone new who is getting up to speed. In a way, walking into a new company is like stepping into a new culture and learning a new language. It takes time and effort to shepherd someone along, but it is worth it and absolutely the right thing to do for your employees.

3. Ingenuity

While I was living in Costa Rica, some policemen threatened me in a transparent effort to elicit a bribe. It was late at night and I was alone in a dark calle in the middle of San Jose.

Although it would have been easy to hand over some cash and head home, I really hate paying bribes. So I stayed calm, complimented their fluency in English, and offered to get them interviews at my company if they let me go. (Back then, British companies paid more than triple a policeman’s salary, so I knew they would be enticed by the idea.). They let me go, and I helped them get interviews a few months later, so it luckily worked out for all of us.

Whether you’re cornered in a dark alley or feeling cornered in a board room, thinking on your feet and coming up with creative solutions can often get you out of a jam. (And in case that doesn’t work, always make sure you have enough cash on hand.)

4. Perspective

Traveling and living abroad have made me a better CEO in the sense that I am always thinking internationally. It’s a cliché, I know, but travel has broadened my horizons and served as a constant reminder that we are living in a global economy.

From the day we launched, our goal was to build the company into an international brand, and we never even considered the alternative. For comparison, I know other CEOs who have never left the country; they tend to think domestically, which could ultimately limit the potential of their businesses.

Technology has made it easier than ever to build multinational companies and, better yet, the rewards will be exponentially bigger if you’re able to serve consumers all around the world.

5. Luck

I once had a run-in with the Colombian Coast Guard off the coast of Cartagena, Colombia. We were shooting a TV commercial on a nearby island and filming had run long, so we were hustling to make it back to shore.

Unbeknownst to us, we were cruising on a passage often used by drug dealers. The Coast Guard suddenly appeared and started screaming at us in Spanish.

The skies had darkened with an impending rainstorm and their boat cast a huge spotlight on us. It was a scene out of Miami Vice. This time, I sensed an impromptu contribution to the Coast Guard’s favorite charity might not extricate us.

Just then the star of our commercial, Natalie París, came up on deck and sauntered into the spotlight. Mouths agape, the Coast Guard crew dropped their weapons and acted like smitten teen-age boys, seeking autographs and photographs. They ended up escorting us back to the dock.

What did I learn here? You can plan and prepare all you want, but luck is important in life and business too. Take it when it comes.

Jen O’Neal is founder and CEO of Tripping.com, which offers vacation homes and short-term rentals. The company is based in San Francisco.